In U.S. Pat. No. 2,767,185 a process is described for the preparation of certain amino cyclanol compounds of the formula ##STR1## wherein n is an integer from 3 to 5, R is a phenyl radical and NR.sub.2.sup.1 is a secondary amino group selected from the class consisting of the N-methyl-N-alkylamino and N-methyl-N-aralkylamino radicals, piperidino, morpholino, pyrrolidino and N'- alkylpiperazino radicals. These compounds, which are produced by the reaction of benzalcyclanones with appropriate secondary amines followed by reduction, were obtained as mixtures of two epimeric racemic modifications, that is a mixture of the racemates of the forms which are denoted cis and trans with respect to the configurations at the asymmetric carbon atoms labeled 2 and 3 in the above formula. Several compounds where NR.sub.2.sup.1 was piperidino or N'-alkylpiperazino were separated into their two racemic modifications without identification. The two additional epimeric racemic modifications which are theoretically possible through opposite configuration at the asymmetric carbon atom labeled 1 were not obtained. The specific utility ascribed to the products in this patent was the use of the N'-alkylpiperazine compounds as intermediates in the preparation of corresponding hexahydro-benzhydryl piperazines whose quaternary salts are stated to be powerful spasmolytics. This utility is further described in U.S. Pat No. 2,748,126, with specific reference to the use of the trans epimer.
In Baltzly, et al., J.A.C.S. 77, 624 (1955) the reaction of secondary amines with benzalcyclanones followed by reduction to afford aminocyclanols is further described, including the characterization by melting point of the cis and trans epimers of piperidino- and N'-alkylpiperazino-benzylcyclohexanols. In russell et al, J.A.C.S. 77, 629 (1955), the method of establishment of the configuration of the epimeric piperidino- and N-alkylpiperazino-benzylcyclohexanols is described.
Huisgen, et al, Chem. Ber. 101, 2043 (1968) described the addition of C-phenyl nitrone to cyclopentene or cyclohexene to give a corresponding isoxazolidine and in the case of the cyclopentene, reduction to afford an .alpha.-methylamino-benzylcyclo- pentanol. The stereochemistry at the .alpha.-carbon atom was not described.